
Windham County long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in Windham County. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Windham County are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Windham County
Showing deals for:8 Feb - 8 Mar
Image gallery for Fabulous 5-bedroom chalet in charming Wilmington perfect for groups

Fabulous 5-bedroom chalet in charming Wilmington perfect for groups
Wilmington
Image gallery for Enchanting 4-bedroom cottage with a view in Weston

Enchanting 4-bedroom cottage with a view in Weston
Weston
Image gallery for Amazing People & Pet-Welcoming Country Haven

Amazing People & Pet-Welcoming Country Haven
Shelburne Falls
Image gallery for Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!

Charming & Cozy River Front Cabin- Close to ski mountains. Ski,Fish,Swim & Hike!
Brattleboro
Image gallery for Leonard’s Log Cabin— Mt. Snow/Stratton Ski House

Leonard’s Log Cabin— Mt. Snow/Stratton Ski House
Wardsboro
Image gallery for Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!

Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!
Chester
Image gallery for Mountain Chalet mins to Mount Snow - Chimney Hill Resort w/indoor pool & hot tub

Mountain Chalet mins to Mount Snow - Chimney Hill Resort w/indoor pool & hot tub
Wilmington
Image gallery for New Lakefront Log Home

New Lakefront Log Home
Wilmington
Image gallery for Okemo Family Friendly Getaway

Okemo Family Friendly Getaway
Ludlow
Image gallery for Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible

Frank Lloyd Wright inspired Private, mountain views, wheelchairs accessible
Weston
Image gallery for Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.

Spacious/Elegant 3 level house on Spruce Lake- swim or fish, short drive to Mt.
Wilmington
Image gallery for Bear Pass Bunkhouse

Bear Pass Bunkhouse
Manchester
Image gallery for Chalet 1mi to Mount Snow with cinema and hot tub

Chalet 1mi to Mount Snow with cinema and hot tub
West Dover
Image gallery for Secluded large country home for big groups with giant open yard for outdoor fun.

Secluded large country home for big groups with giant open yard for outdoor fun.
Whitingham
Image gallery for Quiet Country 2 Bedroom Home Near Bellows Falls & Walpole — Easy I-91 Access

Quiet Country 2 Bedroom Home Near Bellows Falls & Walpole — Easy I-91 Access
Westminster
Image gallery for Renovated Church Sanctuary: Ski and Swim, Relax, Cook, Gather.

Renovated Church Sanctuary: Ski and Swim, Relax, Cook, Gather.
Brattleboro
Image gallery for Beautiful home near Manchester and the Mountains -

Beautiful home near Manchester and the Mountains -
East Arlington
Image gallery for Lovely Chalet, ChimneyHill Community-Clubhouse 2 Pools/Hot tub, Low weekend rate

Lovely Chalet, ChimneyHill Community-Clubhouse 2 Pools/Hot tub, Low weekend rate
Wilmington
Image gallery for Long River House

Long River House
Putney
Image gallery for Year Round Mountain Retreat

Year Round Mountain Retreat
Newfane
Image gallery for SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.

SKIING, PARTY SAFELY IN THE SNOW! NO NEED TO DRINK & DRIVE.
Wilmington
Image gallery for Cozy 2 BR Apartment in Quaint New England Town

Cozy 2 BR Apartment in Quaint New England Town
Walpole
Image gallery for Historic 18th Century Saltbox Farmhouse on Four Acres in heart of Manchester VT

Historic 18th Century Saltbox Farmhouse on Four Acres in heart of Manchester VT
Manchester Center
Image gallery for Beautiful, Historic Year-Round Haven & Vacation Farmhouse

Beautiful, Historic Year-Round Haven & Vacation Farmhouse
Townshend
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Windham County
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Windham County Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Windham County come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Windham County
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Windham County with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Windham County
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Windham County with flexible cancellation policies.